Synthesis of a C22-34 Subunit of the Immunosuppressant FK-506

Journal of Organic Chemistry

Volumn 60, Issue 22, 1995, Pages 7230-7237

  Marshall, James A ^a,b   Xie, Shiping ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOSUPPRESSIVE AGENT; TACROLIMUS;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0028822867     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00127a031     Document Type: Article

References (30)

1. Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J Org. Chem. 1995, 60, 5556.
2. Marshall, J. A.; Perkins, J. F. J. Org. Chem. 1994, 59, 3509.
3. Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1992, 57, 1242.
4. For previous work on the sythesis of FK-506 along these lines, see: White, J. D.; Toske, S. G.; Yakura, T. Synlett 1994, 591 and references cited therein.
5. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
6. Enals 2.2 and 2.3 weee prepared by application of the Corey-Peterson sequence to pentanal and cyclohexanecarboxaldehyde: Corey, E. J.; Enders, D.; Bock, M. G. Tetrahedron Lett. 1976, 7.
7. Schlessinger, R. H.; Poss, M. A.; Richardson, S.; Lin, P. Tetrahedron Lett. 1985, 26, 2391.
8. An analogous sequence has recently appeared for the preparation of (S)-3-butyn-2-ol derivatives: Ku, Y.-Y.; Patel, R. R.; Elisseou, E. M.; Savick, D. P. Tetrahedron Lett. 1995, 36, 2733.
9. Linde, R. G.; Egbertson, M.; Coleman, R. S.; Jones A. B.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 2771.
10. Corey, E. J.; Huang, H.-C. Tetrahedron Lett. 1989, 30, 5235.
11. Marshall, J. A.; Xie, S. J. Org. Chem. 1992, 57, 2987.
12. Xie, S. MS. Thesis, Univeristy of South Carolina, 1992.
13. For a recent review of chiral catalysts employed in [4 + 2] cycloadditions, see: Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129.
14. Wang, Z.-M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302.
15. Saito, S.; Morikawa, Y.; Moriwake, T. J. Org.Chem. 1990, 55, 5424.
16. Gung, B. W.; Melnick, J. P.; Wolf, M. A.; Marshall, J. A. J. Org. Chem. 1994, 59, 5609.
17. Ceder, O.; Hansson, B. Acta Chem. Scand. 1970, 24, 2693.
18. Loncharick, R. J.; Schwartz, T. R.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 14.
19. For a related use of C2-symmetric dispiroketal chiral auxiliaries, see: Bezuidenhoudt, B. C. B.; Castle, G. H.; Geden, J. V.; Ley, S. V. Tetrahedron Lett. 1994, 35, 7451.
20. For additional considerations on the question of acrylate conformation, see: Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
21. Colonge, J.; Crabalona, J. Bull. Chim. Soc. Fr. 1960, 102.
22. The Merck Index, 11th ed.; Budavari, S., Ed.; Merck & Co., Inc.: Rahway, NJ, 1989; p 9105 and references therein.
23. Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418.
24. Jones, A. B.; Villalobos, A.; Linde, R. G., II.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 2786.
25. Unless otherwise stated, 1H and 13C NMR spectra weee determined at 300 and 100.6 MHz, respectively, on dilute solutions of sample in CDCI3. Solvent removal was achieved on a rotary evaporator under aspirator vacuum. For typical experimental protocols, see: Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960.
26. Martin, S. F., Dappen, M. S.; Dupre, B.; Murphy, C. J.; Colapret, J. A. J. Org. Chem. 1989, 54, 2209.
27. Compare: Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkover, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. D. J. Org. Chem. 1986, 51, 2370.
28. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. I. J. Am. Chem. Soc. 1990, 112, 5583.
29. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
30. Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc, Perkin Trans. 1 1985, 2247.